Emiliano Redondi defeated Leonardo Silva 6-4 7-5 in the Bolivia F2 round of 32 on clay. The upset overturned the form book — Leonardo Silva came in leading the head-to-head 1–0, but Emiliano Redondi had been the form player, winning 3 of their last 5 on clay. Emiliano Redondi claimed a first win over Leonardo Silva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-26 | Uruguay F2 | R32 | clay | Leonardo Silva | 6-2 4-6 6-3 |